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Issue 40, 2020
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Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

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Abstract

We report a mild method for the selective deprotection of the N-Boc group from a structurally diverse set of compounds, encompassing aliphatic, aromatic, and heterocyclic substrates by using oxalyl chloride in methanol. The reactions take place under room temperature conditions for 1–4 h with yields up to 90%. This mild procedure was applied to a hybrid, medicinally active compound FC1, which is a novel dual inhibitor of IDO1 and DNA Pol gamma. A broader mechanism involving the electrophilic character of oxalyl chloride is postulated for this deprotection strategy.

Graphical abstract: Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

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Supplementary files

Article information


Submitted
07 May 2020
Accepted
12 Jun 2020
First published
23 Jun 2020

This article is Open Access

RSC Adv., 2020,10, 24017-24026
Article type
Paper

Mild deprotection of the N-tert-butyloxycarbonyl (N-Boc) group using oxalyl chloride

N. George, S. Ofori, S. Parkin and S. G. Awuah, RSC Adv., 2020, 10, 24017
DOI: 10.1039/D0RA04110F

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